There is a known rule that Rishonim cannot argue on the Gemara when it comes to "Halachic" drashos. For example, a Rishon will never give a different answer to a question which the Gemara already answered (Tosfos may ask why the Gemara didn't give that other answer, but he will never give his own answer without more). This is true whether the Gemara's subject is practical Halacha or not.

However, when it comes to aggadic drashos on Tanach, we find Rishonim "disagreeing" with Midrashim and late Acharonim disagreeing on Rishonim. Why do Rishonim feel freer to disagree on an explanation of Chumash than to disagree with a Gemara?

4 Answers
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We do not pose difficulties with [i.e. from] the Aggadah. Are they words of Tradition or expressions of reason? Rather each individual considers their explanation as it seems fit to him. In this [Aggadah] there are no words of Tradition, no prohibition and no license, and no law among the Laws; therefore we do not pose difficulties with it. Should you say to me as many have said to me, “Can it be that you apply the term Aggadah [as pertains to this argument] to words of the Talmud?” It is so; all of these words and those similar to them are Aggadah in their reckoning, whether they be written in books of Derashos, whether they be written in books of Aggadah.

This position is echoed by various Ge'onim and Rishonim; see for example Otzar HaGeonim to Chagigah (pp. 59-60) from R. Hai Gaon and R. Shereira Gaon, and the Ramban in his famous Disputation.

What troubles me with this answer is that the Ramban will knock out Chazal's interpretation in a midrash using logic. If it can be knocked out through logic, why didn't Chazal think of it before choosing that interpretation?
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b aJun 22 '12 at 20:24

@ba Your question refutes itself - because I ask you, based on your own premise, is it possible the rishonim who held this way didn't think of this objection?
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Dov FJun 22 '12 at 20:30

Chazal considered all the problems with an answer (as is evident from the gemara). Saying their reasoning was perfect in halachah but not perfect in agadah is a little inconsistent. But sometimes the truth is inconsistent...
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b aJun 22 '12 at 20:41

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@ba That's a straw man. Who ever said Chazal's reasoning was perfect in halacha? The fact that we do not veer from the psak of the Gemara does not imply this.
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Dov FJun 22 '12 at 20:59

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@ba What are you trying to show from Karisos 12a?
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CuriouserJun 22 '12 at 22:13

The distinction made in Dynamics of Dispute (pages 125 and following) is not halacha vs. aggadta. It is between teachings by Tannaim (of whatever category) that definitely did not originate with Moses' report of G-d's explanation, and all others. Only the former are candidates for dispute. The Rambam certainly maintains that among those teachings, transmitted to and by the Tannaim (as well as Amoraim), are historical accounts and hashkafic ideas that he likewise accepted as fact. (For example, creation ex-nihilo, and the accounts of the Mabul, Avraham's miraculous escape from Nimrod, and the desert wanderings (see Moreh Nevuchim 3:50 and Hilchos Avoda Zorra 1:3)

The main source for the explanation for why Amoraim abstain from disagreeing with Tannaim (when they do) is a passage in the Talmud Yerushalmi on Payah 2:6:

Said Rebbi Zeyra in the name of Rebbi Yochonon: "If you come across a mishna whose reason you cannot understand, do not brush it aside and replace its law with another one. For many laws were told to Moses at Sinai, and all of them are lodged throughout the Mishna."

Said Rebbi Abbin: "How true! For behold the halacha regarding "two varieties of one grain"[as a prime example]! If Nachum HaLavlar had not come and explained to us [that it was a halacha L'Moshe MiSinai], would we ever have known?!"

From this source, one deduces that immediately following the formulation of the Mishna—the time of Rebbi Yochonon, at the beginning of the era of the Amoraim (c. 4000, 250 CE), the tumultuous state of affairs caused an obscurity over which laws had originated with drashos, permitting challenge, and which laws had really originated from Sinai, precluding question.

As summarized in the final paragraph of that chapter,

All details in the Mishna known not to be kabballos, and all
rabbinical decrees not yet voted upon by a Tannaitic Sanhedrin, were
challengeable. On such issues, an Amora could conceivably differ
with a Tanna. As we mentioned above, there were rare instances in
which Amoraim exercised this power.

In defense of YEZ, I never claimed that the distinction was between halacha and agaddta. I did point out that a case of agaddta is used as an example/support, and I pointed out in a parenthetical statement (since it's unrelated to this question) that it applies equally to halacha. I'm not sure how the cited Rambams are relevant, as we are discussing derashos of Chazal.
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YeZMay 19 '14 at 20:33

@YEZ, I was reacting to the statement, "However, in Aggada there is no such concern, and therefore they felt free to argue." Again, the distinction is not between halacha in Aggada, but between that which is definitely not a mesorah and that which might be. This distinction applies as equally to Aggada as to halacha. I cited Rambam because he is the source for the principle that a Beis Din could disagree with an earlier one (in interpreting pesukim), and for whom the question of why Amoraim will not contest Tannaim thereby becomes an issue.
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Zvi LampelMay 20 '14 at 2:04

I was never pinning the distinction on Aggada vs. Halacha, just that Aggada is an example where the principle would apply. Aggada of a drasha from a verse will always fit into that rule. (As opposed to your examples, which is why I identified them as unrelated to this discussion).
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YeZMay 20 '14 at 2:20

(This is a bit surreal for me, arguing with the author of a sefer [which I loved, read and re-read] about if I properly referenced his own sefer)
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YeZMay 20 '14 at 2:57

Thank you for your compliment. It’s interesting to see how one’s ideas come across to others. As to your focus on drash-based Aggada, I see what you're saying. I didn't think the question was dependent upon whether the Aggadic teaching was drasha-based or not. But my point is that Aggadic teachings recognized to represent the consensus of Chazal are not contested, whether or not backed by drashos. So I disagree with the idea that it is justifiable to argue with "essentially any authority in an Aggadic discussion."
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Zvi LampelMay 20 '14 at 3:23

In Dynamics of Dispute, Rabbi Lampel points out that in areas of Aggada, we even find Amoraim breaking the Golden Rule and arguing with Tannaim - see for example Megillah 7a in which Shmuel claims he has a better source for the Divine nature of Megillas Ester:

Said Shmuel: Had I been there, I would have said something better than everything they [the Tannaim] said, as it says etc... Said Rava: All of them [the answers of the Tannaim] have a weakness, but Shmuel's answer does not have a weakness

Rabbi Lampel has a thesis which he uses this to support, namely that the reason in general that Amoraim do not argue with Tannaim is because there was a chain of tradition regarding which halachos were Halacha L'Moshe MiSinai (he proves this with other methods as well), and that chain of tradition was lost in the mayhem of the generation of Rabbi Yehuda HaNasi. Therefore the Amoraim would not argue for fear of inadvertently arguing with a Halacha L'Moshe MiSinai. However, in Aggada there is no such concern, and therefore they felt free to argue. (He also concludes from this thesis that if a given Halacha is clearly not from Sinai, for example if a Tanna had an opinion but then changed his mind about it, then an Amora was free to argue on that Halacha as well, and he cites examples of such.)

This would justify arguing with essentially any authority in a discussion of drash-based Aggada.

Sh'muel does not argue with tanaim (there). He says "were I there, I'd argue" -- but then he'd be a tana.
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msh210♦Feb 28 '14 at 18:13

@msh210 I didn't translate it, but he offers his own opinion. It's like saying "I'm not going to tell you that you're ugly" - it doesn't become that I didn't say it by saying I won't say it. Shmuel said a different opinion not stated by Tannaim. And Rava concluded it was the most solid opinion. This is how R' Lampel takes the Gemara. I personally think the "If I were there" bit is to state that they would have agreed with him.
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YeZFeb 28 '14 at 18:22

@ShmuelBrin arguing about the source of a drasha but supporting the same halacha would further conform to this - as long as you don't risk unintentionally arguing with a halacha l'Moshe mi'Sinai, it's fair game to argue with Tannaim. Especially if the source is explicitly given as not a HL"M
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YeZMar 26 '14 at 22:39

The original question asked was: "[W]hether the Gemara's subject is practical Halacha or not...Why do Rishonim feel freer to disagree on an explanation of Chumash than to disagree with a Gemara?"

I would answer that the project of the rishonim was to distinguish between the lessons in the Chumash that can be procured through the peshat approach, and those that could be procured only through the drash approach. (And each rishon had his own definition of what qualifies as “peshat.”) They were intent in identifying the peshat level of the pesukim. When they differed with a Midrash in interpreting a posuk, they meant the Midrash’s lesson could not be gained through the peshat approach, but at best through the drash-approach. (And sometimes, they tagged the lesson as a minority and even unacceptable opinion, just as can be the case in halacha.)